580566

Tenovin-1

A cell-permeable benzoylthiourea compound that acts as a reversible inhibitor of class III HDAC sirtuins against SirT2 (IC₅₀ = ~ 10 µM).

• Synonym(s): Tenovin-1, N-(4- tert-Butylbenzoyl)-Nʹ-(4-acetylaminophenyl)-thiourea, SIRT2 Inhibitor V, N-(4-tert-Butylbenzoyl)-Nʹ-(4-acetylaminophenyl)-thiourea, SIRT2 Inhibitor V
• Empirical Formula (Hill Notation): C₂₀H₂₃N₃O₂S
• CAS Number: 380315-80-0
• Molecular Weight: 369.48
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• assay: ≥98% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: white
• solubility: DMSO: 5 mg/mL
• shipped in: ambient
• storage temp.: 2-8°C
• InChI: 1S/C20H23N3O2S/c1-13(24)21-16-9-11-17(12-10-16)22-19(26)23-18(25)14-5-7-15(8-6-14)20(2,3)4/h5-12H,1-4H3,(H,21,24)(H2,22,23,25,26)
• InChI key: WOWJIWFCOPZFGV-UHFFFAOYSA-N

Description

General description

A cell-permeable benzoylthiourea compound that acts as a reversible inhibitor of class III HDAC sirtuins (IC₅₀ against SirT2 ~10 µM). Based on studies using the more soluble analog Tenovin-6, Tenovin-1 is expected not to compete with substrate binding and display lower potency against SirT1/3 (IC₅₀ = 21/67 µM using Tenovin-6). Tenovin-1 (10 µM) up-regulates cellular p53 protein, but not mRNA, level in MCF-7 (≥6-fold in 6 h), presumably by blocking mdm2-mediated p53 degradation. Two day Tenovin-1 treatment (10 µM) results in selective killing of cancer cells with functional p53, but not p53-lacking cancer cells or normal human dermal fibroblasts. Despite its low aqueous solubility, administration of Tenovin-1 suspension is shown to effectively reduce BL2 and ARN8 xenographs in mice in vivo (≥50% reduction with 92 mg/kg daily i.p.).

A cell-permeable benzoylthiourea compound that acts as a reversible inhibitor of class III HDAC sirtuins against SirT2 (IC₅₀ = ~ 10 µM). Based on studies using the more soluble analog Tenovin-6, Tenovin-1 is expected not to compete with substrate binding and display lower potency against SirT1/3 (IC₅₀ = 21/67 µM using Tenovin-6). Tenovin-1 (10 µM) up-regulates cellular p53 protein, but not mRNA, level in MCF-7 (≥6-fold in 6 h), presumably by blocking mdm2-mediated p53 degradation. Two day Tenovin-1 treatment (10 µM) results in selective killing of cancer cells with functional p53, but not p53-lacking cancer cells or normal human dermal fibroblasts. Despite its low aqueous solubility, administration of Tenovin-1 suspension is shown to effectively reduce BL2 and ARN8 xenographs in mice in vivo (≥50% reduction with 92 mg/kg, daily, i.p.).

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Lain, S., et al. 2008. Cancer Cell13, 454.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable